Chemistry:Benzyl cyanide

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Benzyl cyanide
Skeletal formula of benzyl cyanide
Ball-and-stick model of the benzyl cyanide molecule
Names
Preferred IUPAC name
Phenylacetonitrile[1]
Other names
Benzyl cyanide[1]
2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
Properties
C8H7N
Molar mass 117.15 g/mol
Appearance Colorless oily liquid
Density 1.015 g/cm3
Melting point −24 °C (−11 °F; 249 K)
Boiling point 233 to 234 °C (451 to 453 °F; 506 to 507 K)
0.1 g/L (25 °C)
log P 1.56
Vapor pressure 1 mmHg (60 °C)
−76.87·10−6 cm3/mol
1.52105 (25 °C)
Hazards[2]
Main hazards Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.
GHS pictograms GHS06: ToxicGHS07: Harmful
GHS Signal word Danger
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NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity (yellow): no hazard codeSpecial hazards (white): no code
1
3
Flash point 102 °C (216 °F; 375 K)[3]
Lethal dose or concentration (LD, LC):
270 mg/kg (rat, oral)
74.982 mg/kg (rat, intraperitoneal)
50 mg/kg (rabbit, subcutaneous)
120 mg/kg (pigeon, intramuscular)
100 mg/m3 (mouse, 2h)
430 mg/m3 (rat, 2h)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

Benzyl cyanide (abbreviated BnCN), also known as phenylacetonitrile, is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry.[4] It is also an important pheromone in certain species.[5]

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide[6] and by oxidative decarboxylation of phenylalanine.[7]

Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.[8]

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid[9] or it can be used in the Pinner reaction to yield phenylacetic acid esters.[10] Hydrogenation gives β-phenethylamine.[11]

The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN.[12] A variety of base-induced reactions result in the formation of new carbon-carbon bonds.[13][14][15]

Uses

Benzyl cyanide is used as a solvent[16] and as a starting material in the synthesis of fungicides (e.g. Fenapanil),[17] fragrances (phenethyl alcohol), antibiotics,[4] and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.[18]

Pharmaceuticals

Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include:[19]

Regulation

Because benzyl cyanide is a useful precursor to numerous drugs with recreational use potential, many countries strictly regulate the compound.

United States

Benzyl cyanide is regulated in the United States as a DEA List I chemical.

China

Benzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021.[33]

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.[4]

See also

References

  1. ↑ 1.0 1.1 Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 16. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. 
  2. ↑ "Phenylacetonitrile" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/Phenylacetonitrile#section=Safety-and-Hazards. 
  3. ↑ "Phenylacetonitrile" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/8794#section=Flash-Point. 
  4. ↑ 4.0 4.1 4.2 Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_363. ISBN 3-527-30673-0. 
  5. ↑ "Toxin Protects Migratory Locusts from Cannibalism". Max Planck Society. 4 May 2023. https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus. 
  6. ↑ Adams, Roger; Thal, A. F. (1922). "Benzyl cyanide". Organic Syntheses 2: 9. doi:10.15227/orgsyn.002.0009. 
  7. ↑ Hiegel, Gene; Lewis, Justin; Bae, Jason (2004). "Conversion of α-Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid". Synthetic Communications 34 (19): 3449–3453. doi:10.1081/SCC-200030958. 
  8. ↑ Wu, Lingyun; Hartwig, John F. (2005). "Mild Palladium-Catalyzed Selective Monoarylation of Nitriles". Journal of the American Chemical Society 127 (45): 15824–15832. doi:10.1021/ja053027x. PMID 16277525. Bibcode: 2005JAChS.12715824W. 
  9. ↑ Adams, Roger; Thal, A. F. (1922). "Phenylacetic acid". Organic Syntheses 2: 59. doi:10.15227/orgsyn.002.0059. 
  10. ↑ Adams, Roger; Thal, A. F. (1922). "Ethyl Phenylacetate". Organic Syntheses 2: 27. doi:10.15227/orgsyn.002.0027. 
  11. ↑ Robinson, John C. Jr.; Snyder, H. R. (1943). "β-Phenylethylamine". Organic Syntheses 23: 71. doi:10.15227/orgsyn.023.0071. 
  12. ↑ Robb, C. M.; Schultz, E. M. (1948). "Diphenylacetonitrile". Organic Syntheses 28: 55. doi:10.15227/orgsyn.028.0055. 
  13. ↑ Makosza, M.; Jonczyk, A (1976). "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses 55: 91. doi:10.15227/orgsyn.055.0091. 
  14. ↑ Itoh, Masumi; Hagiwara, Daijiro; Kamiya, Takashi (1988). "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile". Organic Syntheses 6: 199. doi:10.15227/orgsyn.059.0095. 
  15. ↑ Wawzonek, Stanley; Smolin, Edwin M. (1955). "α-Phenylcinnamonitrile". Organic Syntheses 3: 715. doi:10.15227/orgsyn.029.0083. 
  16. ↑ Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry: 29. doi:10.1002/14356007.a02_355. ISBN 3-527-30673-0. 
  17. ↑ Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_085. ISBN 3-527-30673-0. 
  18. ↑ "PHENYLACETAMIDE". Organic Syntheses 32: 92. 1952. doi:10.15227/orgsyn.032.0092. ISSN 0078-6209. 
  19. ↑ 19.0 19.1 19.2 19.3 19.4 19.5 19.6 William Andrew Publishing (2008). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Norwich, NY: Elsevier Science. pp. 182, 936, 1362, 1369, 1505, 2036, 2157, 2259, 2554, 2620, 2660, 2670, 2924, 3032, & 3410. ISBN 978-0-8155-1526-5. https://books.google.com/books?id=bRX8MwEACAAJ&q=9780815515265. 
  20. ↑ Berkoff, Charles E.; Rivard, Donald E.; Kirkpatrick, David; Ives, Jeffrey L. (1980). "The Reductive Decyanation of Nitriles by Alkali Fusion". Synthetic Communications 10 (12): 939–945. doi:10.1080/00397918008061855. 
  21. ↑ Bub, Oskar; Friedrich, Ludwig (2000). "Cough Remedies". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_013. ISBN 3-527-30673-0. 
  22. ↑ Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_029. ISBN 3-527-30673-0. 
  23. ↑ Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed.. London: Longman Science & Technical. pp. 1174–1179. ISBN 978-0-582-46236-6. https://archive.org/details/TextbookOfPracticalOrganicChemistry5thEd. 
  24. ↑ Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a24_515. ISBN 3-527-30673-0. 
  25. ↑ "a,b-DIPHENYLCINNAMONITRILE". Organic Syntheses 31: 52. 1951. doi:10.15227/orgsyn.031.0052. http://orgsyn.org/demo.aspx?prep=CV4P0387. 
  26. ↑ Dore, J. C.; Gilbert, J.; Bignon, E.; Crastes De Paulet, A.; Ojasoo, T.; Pons, M.; Raynaud, J. P.; Miquel, J. F. (February 1992). "Multivariate analysis by the minimum spanning tree method of the structural determinants of diphenylethylenes and triphenylacrylonitriles implicated in estrogen receptor binding, protein kinase C activity, and MCF7 cell proliferation". Journal of Medicinal Chemistry 35 (3): 573–583. doi:10.1021/jm00081a021. https://pubs.acs.org/doi/abs/10.1021/jm00081a021. 
  27. ↑ Bignon, E.; Pons, M.; Crastes De Paulet, A.; Dore, J. C.; Gilbert, J.; Abecassis, J.; Miquel, J. F.; Ojasoo, T. et al. (September 1989). "Effect of triphenylacrylonitrile derivatives on estradiol-receptor binding and on human breast cancer cell growth". Journal of Medicinal Chemistry 32 (9): 2092–2103. doi:10.1021/jm00129a013. https://pubs.acs.org/doi/abs/10.1021/jm00129a013. 
  28. ↑ 28.0 28.1 "4-Substituted Piperidines. IV. The Synthesis of 4-[(2,6-Dioxo-3-phenyl)-3-piperidylpiperidines"]. Journal of Medicinal Chemistry 11 (4): 797–800. July 1968. doi:10.1021/jm00310a613. https://pubs.acs.org/doi/abs/10.1021/jm00310a613. 
  29. ↑ Daniel Lednicer & L.A. Mitscher drug synthesis Book 3, Page 191.
  30. ↑ Silverman RB, Zieske PA. 1-Phenylcyclobutylamine, the first in a new class of monoamine oxidase inactivators. Further evidence for a radical intermediate. Biochemistry. 1986 Jan 28;25(2):341-6. doi: 10.1021/bi00350a010. PMID: 3955001.
  31. ↑ Singer, T.P. (1987). Perspectives in MAO: past, present, and future. In: Oreland, L., Callingham, B.A. (eds) Monoamine Oxidase Enzymes. Journal of Neural Transmission, vol 23. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8901-6_1
  32. ↑ "1‐Phenylcycloakylamine Derivatives I". Israel Journal of Chemistry 5 (5): 223–229. January 1967. doi:10.1002/ijch.196700039. https://onlinelibrary.wiley.com/doi/10.1002/ijch.196700039. 
  33. ↑ "国务院办公厅关于同意将α-苯乙酰乙酸甲酯等6种物质列入易制毒化学品品种目录的函" (in zh-hans). The State Council - The People's Republic of China. 7 June 2021. http://www.gov.cn/zhengce/content/2021-06/07/content_5615890.htm. 



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